Blasticidin S.

Structural formula
General
Surname	Blasticidin S.
other names	4-Amino-1- (4 - {[(3 S ) -3-amino-5- ( N -methylcarbamimidamido) pentanoyl] amino} -2,3,4-trideoxy-β- D -erythro-hex-2- enopyranuronosyl) -2 (1 H ) -pyrimidinone; 3- (3-Amino-5- (1-methylguanidino) -1-oxopentylamino-6- (4-amino-2-oxo-2,3-dihydropyrimidin-1-yl) -2,3-dihydro- (6H) -pyran-2-carboxylic acid
Molecular formula	C 17 H 26 N 8 O 5
External identifiers / databases
EC number	606-640-2
ECHA InfoCard	100.109.057
PubChem	170012
ChemSpider	148673
Wikidata	Q4925433
properties
Molar mass	422.439 g mol −1
Melting point	235 ° C (dec.)
pK s value	2.4 / 4.6 / 8.0 /> 12.5
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger
H and P phrases	H: 300
	P: ?
Toxicological data	16 mg kg −1 ( LD 50 , rat , oral ) ; 3100 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Blasticidin S is a nucleoside antibiotic and fungicide from Streptomyces griseochromogenes from the group of aminoacyl nucleosides.

properties

Blasticidin S inhibits the translation of eukaryotes and prokaryotes by fixing the tRNA at the P site of the ribosome . Blasticidin S binds copper (II) ions as a chelator . The biosynthesis and total synthesis of blasticidin S have been described. In eukaryotes, blasticidin S is taken up into cells by the protein LRRC8D .

So far, three bacterial resistances to blasticidin S have been described, which are used as selection markers in biochemistry and genetics . The resistance gene bls codes for an acetyltransferase in Streptoverticillum sp. , which also produces Blasticidin S. The bsr gene codes for a blasticidin-S-deaminase in Bacillus cereus and other bacteria. BSD encodes a deaminase in Aspergillus terreus .

Admission

No plant protection products containing this active ingredient are permitted in the EU or Switzerland .

Individual evidence

↑ ^a ^b Entry on Blasticidine. In: Römpp Online . Georg Thieme Verlag, accessed on June 24, 2019.
↑ ^a ^b ^c Entry on Blasticidin-S in the GESTIS substance database of the IFA , accessed on August 28, 2015 (JavaScript required)
↑ Entry on 3- (3-Amino-5- (1-methylguanidino) -1-oxopentylamino-6- (4-amino-2-oxo-2,3-dihydro-pyrimidin-1-yl) -2,3- dihydro- (6H) -pyran-2-carboxylic acid) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ ^a ^b K. Stokowa-Sołtys, M. Jeżowska-Bojczuk: A rice fungicide blasticidin S efficiently binds Cu (II) ions and prevents DNA from metal-induced damage. In: Journal of Inorganic Biochemistry . Volume 127, October 2013, pp. 73-78, doi : 10.1016 / j.jinorgbio.2013.06.014 , PMID 23880034 .
↑ E. Svidritskiy, C. Ling, DN Ermolenko, AA Korostelev: Blasticidin S inhibits translation by trapping deformed tRNA on the ribosome. In: Proceedings of the National Academy of Sciences . Volume 110, number 30, July 2013, pp. 12283-12288, doi : 10.1073 / pnas.1304922110 , PMID 23824292 , PMC 3725078 (free full text).
↑ MC Cone, X. Yin, LL Grochowski, MR Parker, TM Zabriskie: The blasticidin S biosynthesis gene cluster from Streptomyces griseochromogenes: sequence analysis, organization, and initial characterization. In: ChemBioChem : a European journal of chemical biology. Volume 4, Number 9, September 2003, pp. 821-828, doi : 10.1002 / cbic.200300583 , PMID 12964155 .
↑ Y. Ichikawa, K. Hirata, M. Ohbayashi, M. Isobe: Total synthesis of (+) - blasticidin s. In: Chemistry - A European Journal . Volume 10, Number 13, July 2004, pp. 3241-3251, doi : 10.1002 / chem.200305358 , PMID 15224333 .
↑ CC Lee, E. Freinkman, DM Sabatini, HL Ploegh: The protein synthesis inhibitor blasticidin s enters mammalian cells via leucine-rich repeat-containing protein 8D. In: Journal of Biological Chemistry . Volume 289, number 24, June 2014, pp. 17124-17131, doi : 10.1074 / jbc.M114.571257 , PMID 24782309 , PMC 4059153 (free full text).
↑ General Directorate Health and Food Safety of the European Commission: Entry on Blasticidin-S in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 26, 2016.

[römpp-1] Entry on Blasticidine. In: Römpp Online . Georg Thieme Verlag, accessed on June 24, 2019.

[GESTIS-2] Entry on Blasticidin-S in the GESTIS substance database of the IFA , accessed on August 28, 2015 (JavaScript required)

[CLP_100.109.057-3] Entry on 3- (3-Amino-5- (1-methylguanidino) -1-oxopentylamino-6- (4-amino-2-oxo-2,3-dihydro-pyrimidin-1-yl) -2,3- dihydro- (6H) -pyran-2-carboxylic acid) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[PMID_23880034-4] K. Stokowa-Sołtys, M. Jeżowska-Bojczuk: A rice fungicide blasticidin S efficiently binds Cu (II) ions and prevents DNA from metal-induced damage. In: Journal of Inorganic Biochemistry . Volume 127, October 2013, pp. 73-78, doi : 10.1016 / j.jinorgbio.2013.06.014 , PMID 23880034 .

[5] E. Svidritskiy, C. Ling, DN Ermolenko, AA Korostelev: Blasticidin S inhibits translation by trapping deformed tRNA on the ribosome. In: Proceedings of the National Academy of Sciences . Volume 110, number 30, July 2013, pp. 12283-12288, doi : 10.1073 / pnas.1304922110 , PMID 23824292 , PMC 3725078 (free full text).

[6] MC Cone, X. Yin, LL Grochowski, MR Parker, TM Zabriskie: The blasticidin S biosynthesis gene cluster from Streptomyces griseochromogenes: sequence analysis, organization, and initial characterization. In: ChemBioChem : a European journal of chemical biology. Volume 4, Number 9, September 2003, pp. 821-828, doi : 10.1002 / cbic.200300583 , PMID 12964155 .

[7] Y. Ichikawa, K. Hirata, M. Ohbayashi, M. Isobe: Total synthesis of (+) - blasticidin s. In: Chemistry - A European Journal . Volume 10, Number 13, July 2004, pp. 3241-3251, doi : 10.1002 / chem.200305358 , PMID 15224333 .

[8] CC Lee, E. Freinkman, DM Sabatini, HL Ploegh: The protein synthesis inhibitor blasticidin s enters mammalian cells via leucine-rich repeat-containing protein 8D. In: Journal of Biological Chemistry . Volume 289, number 24, June 2014, pp. 17124-17131, doi : 10.1074 / jbc.M114.571257 , PMID 24782309 , PMC 4059153 (free full text).

[9] General Directorate Health and Food Safety of the European Commission: Entry on Blasticidin-S in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 26, 2016.